Flexible Work Arrangements Jobs in Chicago, IL

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Looking for Flexible Work Arrangements jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Arrangements position in the Chicago, IL area.

Teacher (Kindergarten)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

HVAC Service Tech

Company: American Vintage Home

Location: Evanston, IL

Posted Aug 04, 2025

Valid drivers license with a safe driving record. 2+ years of field experience. Diagnose, troubleshoot, and repair HVAC systems, including forced air and…

Security Supervisor

Company: P4 Security Solutions

Location: Rogers Park, IL

Posted Aug 04, 2025

Customer service and front desk reception. The Off Duty or Retired Law Enforcement roles are ideal for those seeking flexible scheduling and premium…

Low-Level C++ Software Engineer

Company: Wolverine Trading

Location: Chicago, IL

Posted Aug 04, 2025

Effective communication skills, with the ability to effectively engage both technical and non-technical stakeholders. Retirement Plans: 401K and Roth 401K.

Plumber - Residential

Company: American Vintage Home

Location: Evanston, IL

Posted Aug 04, 2025

Valid drivers license with a safe driving record. 2+ years of field experience. Ability to troubleshoot, repair, and collect payment.

Co-Teacher (Grade 3)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Automation Support Engineer

Company: Retiina

Location: Forest Park, IL

Posted Aug 04, 2025

Repair and maintain systems in accordance with diagrams, sketches, operation manuals, and manufacturer’s specifications, machinery and mechanical equipment,…

Electrician / Machine Panel wiring (5 yrs ex is +)

Company: Automatic Liquid Packaging Solutions, LLC (ALPS)

Location: Arlington Heights, IL

Posted Aug 04, 2025

Ability to read and understand electrical control schematics and drawings(ladder diagrams) and mechanical layouts. Pay: $27.00 - $32.00 per hour.

Accountant

Company: Cushman & Wakefield

Location: Chicago, IL

Posted Aug 04, 2025

May be assigned to either accounts payable or receivable and may handle billing/invoicing, cash receipts, data entry, budgets and budgeting, expenses, sales…

Contact Center Rep I

Company: Advocate Aurora Health

Location: Oak Brook, IL

Posted Aug 04, 2025

Major Responsibilities: Customer Care and Service Excellence 1)Promptly answers all incoming calls and other contact methods with the standard professional…

Maintenance Employee

Company: De LaSalle Institute

Location: Chicago, IL

Posted Aug 04, 2025

Resource room and faculty dining room.  Responsible for the cleanliness of offices, classrooms, executive office washrooms, faculty.

Teacher (Kindergarten)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 04, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Frequently Asked Questions

What are typical salary ranges by seniority for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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